1-Aryl-4-pyridones

Abstract

Compounds of the formula ##STR1## wherein R 1 is carboxy, carboxylate, carbalkoxy, carbamoyl or cyano, R 2 is alkyl, R 3 is hydrogen or alkyl, R 4 is hydrogen, alkyl, or halogen and R 5 is phenyl or substituted phenyl, Are active as plant growth regulators, and particularly as chemical hybridization agents.

I claim: 
     
       1. A method of inducing male sterility in a cereal grain plant which comprises treating the plant prior to meiosis with an amount effective to produce male sterility in the plant of a compound of the formula ##STR10## wherein R 1  is a carboxy group or an agronomically-acceptable salt thereof, a carb(C 1  -C 4 )alkoxy group, a carbamoyl group, a (C 1  -C 4 )alkyl or di(C 1  -C 4 )alkyl carbamoyl group, or a cyano group, R 2  is a (C 1  -C 4 )alkyl group,   R 3  is a hydrogen atom or a (C 1  -C 4 )alkyl group,   R 4  is a hydrogen atom, a (C 1  -C 4 )alkyl group, or a halogen atom, and   R 5  is an unsubstituted phenyl group or a substituted phenyl group having up to three substituents having a total of up to 6 carbon atoms.   
     
     
       2. A method of producing hybrid cereal grain seed which comprises treating a female parent of the cereal grain prior to meiosis with a compound of the formula ##STR11## wherein R 1  is a carboxy group or an agronomically-acceptable salt thereof, a carb(C 1  -C 4 )alkoxy group, a carbamoyl group, a (C 1  -C 4 )alkyl or di(C 1  -C 4 )alkyl carbamoyl group, or a cyano group, R 2  is a (C 1  -C 4 )alkyl group   R 3  is a hydrogen atom or a (C 1  -C 4 )alkyl group,   R 4  is a hydrogen atom, a (C 1  -C 4 )alkyl group, or a halogen atom, and   R 5  is a phenyl group or a substituted phenyl group having up to three substituents having a total of up to 6 carbon atoms, in an amount sufficient to produce male sterility in the female parent, causing the female parent to be pollinated with pollen from a male parent of the cereal grain, allowing the female parent to mature until seed formation is substantially complete, and harvesting the mature seed from the female parent.     
     
     
       3. A composition for inducing sterility in cereal grain plants which comprises an effective amount of a compound of the formula ##STR12## wherein R 1  is a carboxy group or an agronomically-acceptable salt thereof, a carb(C 1  -C 4 )alkoxy group, a carbamoyl group, a (C 1  -C 4 )alkyl or di(C 1  -C 4 )-alkyl carbamoyl group, or a cyano group, R 2  is a (C 1  -C 4 )alkyl group,   R 3  is a hydrogen atom or a (C 1  -C 4 )alkyl group,   R 4  is a hydrogen atom, a (C 1  -C 4 )alkyl group, or a halogen atom, and   Z is a substituted phenyl group having up to three substituents selected from halogen atoms, (C 1  -C 4 )alkyl groups, (C 1  -C 4 )alkoxy groups, trifluoromethyl groups, and nitro groups, or, when R 3  is a hydrogen atom, additionally an unsubstituted phenyl group, and an agronomically-acceptable carrier.   
     
     
       4. The method of claim 1 wherein R 1  is a carboxy group or an agronomically-acceptable salt thereof. 
     
     
       5. The method of claim 4 wherein R 2  is a methyl group and R 4  is a hydrogen atom. 
     
     
       6. The method of claim 5 wherein R 3  is a methyl group. 
     
     
       7. The method of claim 6 wherein Z is a halophenyl group. 
     
     
       8. The method of claim 7 wherein Z is a 4-halophenyl group. 
     
     
       9. The method of claim 7 wherein Z is a 3-halophenyl group. 
     
     
       10. The method of claim 6 wherein Z is a trifluoromethylphenyl group. 
     
     
       11. The method of claim 5 wherein R 3  is a hydrogen atom. 
     
     
       12. The method of claim 4 wherein R 2  is a methyl group and R 4  is a halogen atom. 
     
     
       13. The method of claim 12 wherein R 3  is a methyl group.